Stereoelectronic Effects in Multivicinal Fluoroalkanes and Conformational Implications

Autor(es)

Simoes, Luis H. ^[1] ; Cormanich, Rodrigo A. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, Dept Organ Chem, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2020, n. 4 JAN 2020.
• Citações Web of Science: 0

Resumo

Multivicinal fluoroalkanes is an interesting group of fluorinated compounds whose synthesis have been extensively explored, but it lacks theoretical studies to support and understand experimental evidences about their geometry. This work elucidates the effects that rule multivicinal fluoroalkanes preference for helical character in extended geometries. Molecules chosen as models are all-syn and all-anti multivicinal fluorinated n-alkanes containing 4-10 carbon atoms. Natural Bond Orbitals (NBO) calculations point out that the main driving force to helical conformation in multivicinal fluoroalkanes is electrostatics, in opposition to hyperconjugation domination in n-perfluoroalkanes. Also, these theoretical calculations show F-H attractive interactions as the main important ones in helical stabilization, particularly those at 1,5 relative distance. (AU)

• Processo FAPESP: 18/03910-1 - Estudos físico-químicos de compostos orgânicos fluorados: abordagens experimental e teórica
• Beneficiário: Rodrigo Antonio Cormanich
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores